Exploring Lost Opportunities with Time Travel and Thrilling Encounters

For once, I didn’t feel like immediately returning home. As I looked down at Stephanie’s naked, petite body, I knew I had to at least experience a little more of what things could have been like. I kissed her one more time and stepped out of the shower, drying off with one of the towels and getting dressed. As I walked out of the room I was greeted by Allie.

“Way to go stud” she smirked and applauded. “That sounded like quite the performance.”

“I don’t think Stephanie will disagree” I chuckled in response.

“Definitely not” Stephanie laughed as she emerged, dressed in just her underwear.

“I knew it was only a matter of time for you two” Allie laughed.

“Do you want to stay over tonight?” Stephanie asked, biting her lip.

“Sounds like a plan” I smiled.

“Wait a second guys” Allie said. “I have a test tomorrow and I need some sleep. I can’t have you guys keeping me up all night.”

“Oh don’t be jealous” Stephanie laughed. “We’ll hold it down.”

The three of us watched some television and snacked for a while. Finally Allie got up and turned to her room.

“Remember, keep it quiet” she winked and disappeared into her room.

“Should we turn in too?” Stephanie asked with a laugh.

I nodded and we made our way into Stephanie’s room. She didn’t have the largest bed, but that just made things more compact for us. I sat down on her bed and Stephanie started taking her clothes off.

“I hope you don’t mind, but I sleep naked” she grinned as she was already down to underwear again.

“I don’t always sleep naked, but when I do, it’s when I’m with you” I quoted partially from a commercial that was stuck in my head from my current time.

“What the hell are you talking about?” Stephanie laughed.

“Oh, nothing” I laughed too, realizing that commercial was still years away.

I started to take my shirt off, and by the time it was over my head, Stephanie was next to me, completely naked. She watched eagerly as I removed my bottoms and boxers, revealing my once again painful erection. She giggled a little and brushed it, gently letting her fingers run over me.

“How about a little game?” I smiled.

“What did you have in mind?” she asked, hand still teasing me.

“Let’s do a little 69” I started. “Whoever makes the other cum first gets to decide what position we fool around in next.”

She grinned excitedly and quickly got into position. Without warning, she plunged her mouth down on my cock, sucking eagerly and pumping my shaft up and down.

“Okay, go” she giggled a few seconds later. I laughed before parting her pussy lips with my fingers and quickly starting to lick her clit. A few seconds later, I pushed two fingers into her tight pussy and curled them against her g-spot. That started her moans, increasing in frequency and intensity as she tried to take more of my cock down her throat. I wrapped my lips around her clit and started to suck on it as my fingers rubbed her g-spot over and over. From the intensity of her moans, I knew I was in good shape to win this. I felt her trying to pull herself off my mouth.

“Oh no you don’t” I grinned and grabbed her tight ass, forcing her pussy right back into my mouth, sucking and lapping at her clit furiously, as my fingers continued to work their magic.

“Oh fuck” she shrieked as I could already feel her tensing up. My tongue danced across her clit without resting and I could feel the vibrations increasing on my cock. She rubbed my balls, trying to bring me closer, though I knew she wasn’t going to get there in time. She confirmed that by giving up on her pursuit and putting her face on my thigh.

“Fuck, fuck!” she screamed as she hit her climax, her pussy muscles clamping down on my fingers. She shook on top of me as I smiled against her pussy and licked her through her powerful orgasm.

“Guess it’s your choice” she panted, trying to come down from her high.

“Well, I need a few minutes anyway, so let me think about it” I laughed and invited her to rest in my arms. As she laid with me, I let my hands roam her petite body, feeling the soft skin of her thighs, arms and body. She hugged me tightly, and this was yet another time where the device was leading towards reflection. It wasn’t easy to see how much fun I could have had, on a pretty regular basis, nonetheless. Still, I was thankful to at least be getting a glimpse. I blew a lot of great opportunities, but I don’t know anyone else that got a chance to go back and re-do them, even temporarily.

“Okay, let’s do this” I smiled after a while. I helped Stephanie onto her hands and knees, and she got into position when she realized what I was doing. I stared at her tight, firm ass and got behind her, pressing my cock against her lips. She moaned and my hands rubbed up and down her back. I gripped my cock and found her opening, shoving my length inside and spreading her walls again as I entered. I could feel my cum from earlier giving me extra lubrication as I quickly started to pick up a fast rhythm.

“Oh fuck yeah” Stephanie moaned as each powerful thrust from my end made her ass jiggle lightly. I reached around and cupped her perky breasts, playing with her nipples as I worked my way in deeper. I could feel myself sliding against her g-spot, and Stephanie started to play with her clit. It wasn’t long before she climaxed, squeezing her tight muscles around my cock as she moaned in ecstasy. I grabbed her hips and started to bounce into her harder. Our bodies started to make slapping sounds as they came together roughly.

“Shut up you guys!” I heard Allie yell from outside. That made both of us laugh, and I took a hand and came around in front of Stephanie’s face, putting it against her mouth. Her moans were muffled but it seemed to turn her on as she bounced back against me harder, meeting my thrusts. I felt her mouth open against my hand as she started to cum again, another series of spasms going off around my cock. All of the rough orgasms she continued to have were taking their toll on my stamina, forcing ahead the timeline of mine. As I started to get stiffer inside of her, she brought one of her hands back to rub my balls. My thrusts got wilder and more desperate as I neared the finish. Her hands and fingers worked on my balls, bringing the rush on just a little quicker. A few more thrusts and I knew I was there. I pushed myself deep inside her and waited that extra second that happens sometimes before a powerful orgasm. She continued to rub me and then I felt the first twitch as cum streamed out in fast, thick ropes inside her. I shook and bucked against her as I couldn’t seem to unload myself quickly enough. I pulsed and spasmed and felt myself emptying everything I had inside Stephanie’s depths. I ended up falling on top of her, still buried inside, as the last twitches sent a little more of my seed inside her.

We laid like that for a bit until we both regained control of our breathing. Then she flipped over and kissed me hard, running her hand through my hair. We laid there until we both fell asleep. The next thing I knew, the sun was out and it was actually time to get ready for classes. I couldn’t see going through a day of school, and any more of this experience was just going to show me more of what could have been. I went over to my clothes and took out the device. I turned it over and my eyes widened as I noticed the faces of every girl that I had been with during my trips back were now engrained on the device. I didn’t know what it meant, but my heart raced at the idea that there was something I didn’t quite understand going on.

I took a deep breath and pressed the button. The familiar flash of light filled the room and I was back home, once again. Another line disappeared from the device, leaving just three remaining. I turned it over and noticed Stephanie’s face was now there, right after Kaylee’s picture. What in the world did it mean? I guess it could mean nothing, and was simply another form of tracking, just like the lines. I touched the faces of the girls, and nothing happened. I ran my finger across the three remaining lines; nothing happened. I shrugged my shoulders and put the device down.

“Three left” I said out loud. “Damn it.” I looked at my list of potential choices and knew there was at least six or seven very worthy possibilities. The only way this was going to work was to get a little creative. The rules of the device said that I could go back ten times. That means, if I could work multiple situations into the same trip back, I could possibly attack this list a little more completely. The only problem with that, was I could only go back to a specific time, so if I wanted to do more than one experience, it would need to be with two girls that I was exploring at the same time. I also might not have an in because I wouldn’t be able to go back to a specific opening from more than the first choice, as I had been doing.

I started to group my list. I split it into high school and college acquaintances. I looked to see if any of the girls even knew each other. There were two that I had definitely decided I was going to go back and try, so that meant this was the last real toss up.

So far, I had really only concentrated on friends. That was a safer option, but it also meant I was missing out on some potentially exciting, more spontaneous encounters. There was more than one time, mainly during college, where I talked to a girl who I really didn’t know after class. It was always exciting, but I knew I could never explore things further. I could try going back to one of these moments, and then try to find another during the same trip. There were two specific times that came to mind.

I remember being in a really difficult science class at one point. The teacher was difficult to understand and the subject material was rough. There was a blonde girl with those trendy glasses who was probably model material. After a particularly tough lecture, we went to the local Starbucks and talked for a while. She gave me her number, and it remained uncalled in my contacts list for years until I deleted it.

The other situation that stood out was from one of my night classes. If I remember, the class was fun, but long, and there were two girls (they were friends) that I had only briefly gotten to know during the year. One had brown hair and soft blue eyes, with light skin and average height, while the other had darker brown hair, green eyes, with more tanned skin and was shorter. For some reason, during one of the last classes of the semester, the three of us walked out together and talked for a while. I was making them laugh with some of my impressions and eventually one of them gave me her number (and took mine) and told me we should get together during the winter break. That, of course, never came to be, either.

As I thought about it, it occurred to me that, of course, these happened years apart. There was no way I could put myself back and get near both of these events. I laid there for a while before I had a brainstorm. I could go back to the later of the two events, which was the incident with the two girls. I could play that out, and then call the girl from the Starbucks day. It might result in an extended trip, and who knows if the first girl would even remember me, but it was the only chance to get both of those in during the same visit.

I grabbed the device and pressed the button. A normal time of light flashed as I went back about four years again. There I was, walking out of class, talking to the two girls. Kacey was the fairer skinned girl and Nicole was the more tanned one. As we laughed and joked, I remembered back to how good I felt about myself that night, keeping the attention of these two beauties.

All of a sudden it dawned on me and I cursed myself in my head. Yes, this was the scene in my mind, and the last time I had ever really talked to either of the girls, but there was no set up that night. We talked about doing something that winter break. As much fun as it was to re-live some of these moments, I really didn’t want to be trapped here for weeks, even if it wouldn’t cost me much current time. I had to do my best to push up the time line of this encounter. As we approached the point where we went our separate ways, Nicole took her phone out, just as she had done.

“Let me get your number” she smiled. “We should totally do something this winter break.”

“Yeah definitely” I responded and gave her my number. “You know, we could do something sooner if you guys are free.”

“Oh?” Nicole smiled again. “What did you have in mind?”

“Anything where we can all hang out and get to know each other more” I answered.

Nicole exchanged a glance with Kacey. “Why don’t you come by our apartment complex tomorrow?”

“Sounds fine” I said, careful not to sound overly excited.

“Great, see you tomorrow” Nicole said and we separated. Now I had a day to kill in the past. I couldn’t make any gains in the present, so this was probably going to be a waste of time. I decided to walk around campus for a while and see if I could bring back some more memories. I saw the spot that I ate lunch and the building that I had most of my classes. I even recognized the occasional passing face.

I let out a deep breath and grumbled a little. The point of the device wasn’t to keep me trapped here waiting for situations to happen over time. I looked down at the floor and a few seconds later ended up bumping into someone.

“Oh I’m sorry” I said as I looked up. “Leslie?”

“Hey!” Leslie laughed and hugged me. “Oh my gosh, it’s been so long. How have you been?”

“Good, good” I laughed. Leslie was one of my more long term friends at college. She had black hair, brown eyes, and was very busty. I had always guessed that she was in the larger C range. She was a smart girl but was always kind of ditzy. I always thought she would be the type of girl who would do anything if you made a convincing enough argument.

“What are you doing tonight?” I asked her with a grin.

“I was just planning on doing some studying” she responded.

“You have to hang out with me” I said. “It’s been way too long.”

“What did you want to do?” she asked.

“To be honest” I started with a smile. “I’ve always wanted to sneak into the school pool after hours.”

“What?!” she said in her over exaggerated tone and laughed.

“Yeah, let’s have some fun!” I said excitedly, grabbing her hand and pulling her towards the pool. “Let’s not even get bathing suits. Let’s just go in in our underwear.”

“You’re crazy!” she laughed, scooting along with my pulling. Before long, we were just outside the fence of the pool on campus. Everything was pretty dark. The fence wasn’t all that high, and I easily pulled up and over it. I helped Leslie get over it, too, and we stood next to the pool. I started to take my shirt off and urged Leslie to join me. There wasn’t a lot of light but there was enough to see. I was really curious to see her without a shirt on, and I felt my heart rate increase when she grabbed her shirt and pulled it off. Her breasts looked even bigger than I had thought as they sat in a sexy blue bra. Soon, we were both in our underwear. I knew making a ton of noise would be a bad idea, so I quietly walked down the steps of the pool. It was a little cooler than I had hoped, but still maintained a little warmth from the day and heater.

“Come on!” I said in a hushed tone. Leslie giggled and then made her way into the pool with me.

“It’s cold!” she whispered.

“I’ll keep you warm” I chuckled and grabbed onto her, wrapping my arms around her body and my legs around her hips from the side of her. I pretended to lose my balance and grabbed onto her breasts to keep me from falling.

“I’m sorry!” I whispered to her. I breathed easier when she laughed.

“Oh it’s ok, they always get in the way” she giggled.

“I have to admit” I said, unwrapping myself from her and standing in front of her. “I’ve always been kind of attracted to you.”

“Really?” she asked, seemingly surprised. She gasped slightly when I slipped my finger underneath one of her bra straps and pulled it off of her shoulder. I did the same to the other strap and her bra lost its support, sliding off her large breasts. I immediately had to grab them, their fullness just fitting into my hands. Her nipples were hard, either from the water or, I hoped, from getting turned on. I moved my face down and took her breasts into my mouth. I sucked on their fullness and made sure to dance my tongue across her hard nipples. She was moaning slightly and hanging onto my hair.

“Let’s move this out of the water” I suggested, helping the two of us rise up on the edge. After I played with her breasts a little more I got bolder. “Leslie, you have to let me titty fuck you. I’ve wanted it for so long.”

She must have been at least a little turned on because she nodded. I slid off my boxers and smiled as I heard the familiar gasp when she saw my size. She got up onto her knees and pushed her large breasts together with a smirk. I angled myself towards her and got my length between her breasts. Most girls struggled to pull this off with me, but Leslie engulfed my shaft, and the water from the pool helped her a little with lubrication. I thrusted between her large breasts and she moved them with me. Sometimes, she licked my tip when it popped through. I held onto her shoulders and head for support as I let myself fuck her chest quicker. Occasionally, I would drop one of my hands onto her breasts so I could grab them and enjoy their size. One time I popped through her breasts, she sucked down on my head and swirled her tongue around, starting to build me.

As soon as I felt myself starting to get that familiar feeling, I really got into it, thrusting roughly between her chest. I had my hands on her shoulders now to support both of us as I picked up the pace. She took my head into her mouth again and sucked for a few seconds, and I could feel myself getting stiffer. She took her mouth off of me just in time, as I hit my climax and started to shoot big ropes of hot cum all over her face and chin. She shrieked slightly as my big load hit her, but I continued to fuck her breasts, relishing the experience. As my orgasm started to slow down, I took my cock from between her chest and shot the last of my load onto her breasts.

“Wow, that was a lot” she giggled and rubbed my leg.